1-[N.sup.2 -(10,12-dimethyl-1-oxo-tetradecyl) ornithine]-4-[4-(4-hydroxyphenyl)-2-aminobutanoic acid]-5-(3-hydroxyglutamine)echinocandin B having the formula ##STR1## (hereinafter Compound I) and useful as an antibiotic agent as described and claimed in copending application Ser. No. 374,418, filed Jun. 30, 1989 and in copending application Ser. No. 492,025, filed Mar. 12, 1990 is normally produced as one of the minor components on the cultivation of MF 5171 Zalerion arboricola ATCC 20868.
Compound I is a white solid having the following spectral characteristics:
MASS SPECTRAL DATA
Electron impact (EI) mass spectral data were obtained on a Finnigan-MAT 212 mass spectrometer at 90 eV. Gas Chromatograph-Mass Spectrogram (GC-MS) analyses of the TMS (trimethylsilyl) derivatives of total acid hydrolysates were performed on the same instrument. Fast atom bombardment (FAB) mass spectra were recorded on a VG20-253 or Finnegan MAT 90 instrument.
Compound I has a molecular weight 1014 by FAB-MS (observed (M+Na).sup.+ at m/z 1037). GC-MS of the total acid hydrolysate disclosed one equivalent each of threonine, 4-hydroxyproline, 3-hydroxy-4-methylproline, 3-hydroxyglutamic acid, and a C16:0 saturated fatty acid. The HR-FAB-MS from [M+Cs].sup.+ ion indicates the molecular formula to be C.sub.51 H.sub.82 N.sub.8 O.sub.13 (Calcd. 1014.6001, Found 1014.5915.)
NMR SPECTRAL DATA
.sup.1 H and .sup.13 C NMR spectra were recorded in CD.sub.3 OD at ambient temperature on Varian XL300 and XL400 spectrometers. Chemical shifts are indicated in upper relative to TMS at zero ppm using the solvent peak at .delta.3.30 and 49.0 ppm as internal standards for .sup.1 H and .sup.13 C NMR spectra respectively.
Compound I
.sup.1 H NMR Spectrum in CD.sub.3 OD at 400 MHz is seen in FIG. 1.
.sup.13 C NMR Chemical Shifts: obtained in CD.sub.3 OD at 100 MHz.
11.2, 11.6, 19.8, 20.2, 20.7, 24.6, 27.0, 28.0(2.times.), 30.27, 30.33, 30.5, 30.7, 31.1, 31.2, 32.9(2.times.), 33.9, 36.7, 38.0, 38.3, 38.5, 39.0, 40.1, 45.9, 52.8, 53.0, 55.2, 55.7, 57.1, 58.6, 62.1, 68.2, 70.3, 70.7, 71.3, 76.0, 116.3(2.times.), 130.5(2.times.), 133.0, 156.7, 170.2, 172.2, 172.7, 173.60, 173.63, 175.2, 176.3, 176.5 ppm.
It has however not been possible to produce it in a significant amount or in an amount to exceed Compound X of the following structure: ##STR2## (Compound X is the major metabolite of naturally occurring Zalerion arboricola, ATCC 20868. It is described and claimed in application Ser. No. 362,647, filed Jun. 7, 1989 now U.S. Pat. No. 4,931,352, Jun. 5, 1990 which is a continuation of Ser. No. 105,795 filed Oct. 7, 1987, now abandoned.)